Hydrochloric Acid → 5-(Benzyloxy)-1-methyl-4-oxo-1,4-dihydropyridine-2-carboxylic acid

HRID 913008Notes

Reaction equation

HRID 913008 reaction equation
[CH2:1]([O:8][C:9]1[C:10](=[O:18])[CH:11]=[C:12]([C:15]([OH:17])=[O:16])O[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:19][NH2:20].CO.Cl>>[CH2:1]([O:8][C:9]1[C:10](=[O:18])[CH:11]=[C:12]([C:15]([OH:17])=[O:16])[N:20]([CH3:19])[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 6329MethylamineHCID 64807825-(benzyloxy)-4-oxo-4H-pyran-2-carboxylic acid

Product 1

HCID 154622955-(Benzyloxy)-1-methyl-4-oxo-1,4-dihydropyridine-2-carboxylic acidYield 90%

Procedure

A mixture of 5-benzyloxy-4-oxo-4H-pyran-2-carboxylic acid (20.0 g, 81.2 mmol) and a solution of 2M MeNH2 in methanol (162.5 mL, 325 mmol) was stirred at RT for 16 h. Volatiles were removed under reduced vacuum, and the residue was dissolved in 70 mL of de-ionized water. To the ice-cold mixture was added a 6N HCl solution (13.5 mL, 81.0 mmol) dropwise. The precipitated solid was collected via filtration, and washed with water and acetone to give the title compound as a light yellow solid (18.9 g, 90% yield). 1H NMR (400 MHz, DMSO-D6) δ (ppm): 7.82 (s, 1H), 7.45-7.33 (m, 5H), 6.72 (s, 1H), 5.05 (s, 2H) and 3.84 (s, 3H); MS-ESI (m/z): 259.8 [M+1]+, 91.2.

Workup

  1. customVolatiles were removed under reduced vacuum
  2. dissolutionthe residue was dissolved in 70 mL of de-ionized water
  3. filtrationThe precipitated solid was collected via filtration
  4. washwashed with water and acetone

Sources & evidence

ORD record
ord-46cc1209434946bd9a974c48fb76e2ef
Source dataset
uspto-grants-2011_09
Patent number
US08026261B2

Reaction notes

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